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Nitrogen Mustard Based 2-Benzylidene-1-tetralone as ICT-Based Fluorescent Probe for Drug Release Monitoring and Cervical Cancer Therapy

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Abstract

A series of novel intramolecular charge transfer (ICT) based 2-benzylidene-1-tetralones that contain nitrogen mustard for drug release monitoring and cervical cancer therapy were developed. Their emission wavelength and Stokes shift were up to 550 nm and 142 nm, respectively. These compounds exerted excellent anticancer activity against cervical cancer cells, among which 2-{4-[bis(2-chloroethyl)amino]benzylidene}-7-fluoro-3,4-dihydronaphthalen-1(2H)-one exerted the strongest anti-proliferation activity that inhibited HeLa cell cycle in G2/M phase and induced cell apoptosis, as well as activating pro-apoptotic proteins. Furthermore, the release of 2-{4-[bis(2-chloroethyl)amino]benzylidene}-7-fluoro-3,4-dihydronaphthalen-1(2H)-one probe was monitored to locate in lysosomes and nuclei.

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REFERENCES

  1. Arnold, C., Nat. Med., 2022, vol. 28, p. 606. https://doi.org/10.1038/s41591-022-01759-6

    Article  CAS  Google Scholar 

  2. Cheng, H.-B., Qiao, B., Li, H., Cao, J., Luo, Y., Kotraiah Swamy, K.M., Zhao, J., Wang, Z., Lee, J.Y., Liang, X.-J., and Yoon, J., J. Am. Chem. Soc., 2021, vol. 143, p. 2413. https://doi.org/10.1021/jacs.0c12851

    Article  CAS  Google Scholar 

  3. Liu, L., Liu, F., Liu, D., Yuan, W., Zhang, M., Wei, P., and Yi, T., Angew. Chem. Int. Ed Engl., 2022, vol. 61, p. e202116807. https://doi.org/10.1002/anie.202116807

  4. Paul, A., Biswas, A., Sinha, S., Shah, S.S., Bera, M., Mandal, M., and Singh, N.D.P., Org. Lett., 2019, vol. 21, p. 2968. https://doi.org/10.1021/acs.orglett.9b00124

    Article  CAS  Google Scholar 

  5. Paul, A., Mengji, R., Bera, M., Ojha, M., Jana, A., and Singh, N.D.P., Chem. Commun. (Camb), 2020, vol. 56, p. 8412. https://doi.org/10.1039/d0cc03524f

    Article  CAS  Google Scholar 

  6. Pena, A.-M., Chen, X., Pence, I.J., Bornschlögl, T., Jeong, S., Grégoire, S., Luengo, G.S., Hallegot, P., Obeidy, P., Feizpour, A., Chan, K.F., and Evans, C.L., Adv. Drug Deliv. Rev., 2020, vol. 153, p. 147. https://doi.org/10.1016/j.addr.2020.03.003

    Article  CAS  Google Scholar 

  7. Zuo, M., Zhou, J., Yu, J., and Cui, S., Russ. J. Inorg. Chem., 2021, vol. 66, p. 982. https://doi.org/10.1134/S0036023621070159

    Article  Google Scholar 

  8. Kovalev, V.V., Kokunov, Y.V., Shmelev, M.A., Voronina, Yu.K., Kiskin, M.A., Popov, L.D., and Eremenko, I.L., Russ. J. Coord. Chem., 2021, vol. 47, p. 272. https://doi.org/10.1134/S1070328421040047

    Article  CAS  Google Scholar 

  9. Follen, M., Levenback, C.F., Iyer, R.B., Grigsby, P.W., Boss, E.A., Delpassand, E.S., Fornage, B.D., and Fishman, E.K., Cancer, 2003, vol. 98, p. 2028. https://doi.org/10.1002/cncr.11679

    Article  Google Scholar 

  10. Callmann, C.E., LeGuyader, C.L. M., Burton, S.T., Thompson, M.P., Hennis, R., Barback, C., Henriksen, N.M., Chan, W.C., Jaremko, M.J., Yang, J., Garcia, A., Burkart, M.D., Gilson, M.K., Momper, J.D., Bertin, P.A., and Gianneschi, N.C., J. Am. Chem. Soc., 2019, vol. 141, p. 11765. https://doi.org/10.1021/jacs.9b04272

    Article  CAS  Google Scholar 

  11. Dora, N.O., Blackburn, E., Boles, J.E., Williams, G.T., White, L.J., Turner, S.E. G., Hothersall, J.D., Askwith, T., Doolan, J.A., Mulvihill, D.P., Garrett, M.D., and Hiscock, J.R., RSC Adv., 2021, vol. 11, p. 14213. https://doi.org/10.1039/d1ra02281d

    Article  CAS  Google Scholar 

  12. Lipska, K., Gumieniczek, A., Pietraś, R., and Filip, A.A., Molecules, 2021, vol. 26. https://doi.org/10.3390/molecules26102903

  13. Jana, A., Baruah, M., Munan, S., and Samanta, A., Chem. Commun. (Camb), 2021, vol. 57, p. 6380. https://doi.org/10.1039/d1cc02600c

    Article  CAS  Google Scholar 

  14. Kong, X., Li, M., Dong, B., Yin, Y., Song, W., and Lin, W., Anal. Chem., 2019, vol. 91, p. 15591. https://doi.org/10.1021/acs.analchem.9b03639

    Article  CAS  Google Scholar 

  15. Long, Y., Liu, J., Tian, D., Dai, F., Zhang, S., and Zhou, B., Anal. Chem., 2020, vol. 92, p. 14236. https://doi.org/10.1021/acs.analchem.0c03490

    Article  CAS  Google Scholar 

  16. Shang, J., Li, Y., Chen, K., and Li, H., J. Fluoresc., 2021, vol. 31, p. 755. https://doi.org/10.1007/s10895-021-02702-7

    Article  CAS  Google Scholar 

  17. Zhu, M., Xu, Y., Sang, L., Zhao, Z., Wang, L., Wu, X., Fan, F., Wang, Y., and Li, H., Environ. Pollut., 2020, vol. 256, p. 113427. https://doi.org/10.1016/j.envpol.2019.113427

    Article  CAS  Google Scholar 

  18. More, G.S., Thomas, A.B., Chitlange, S.S., Nanda, R.K., and Gajbhiye, R.L., Anticancer. Agents Med. Chem., 2019, vol. 19, p. 1080. https://doi.org/10.2174/1871520619666190305141458

    Article  CAS  Google Scholar 

  19. Chen, W., Fan, H., Balakrishnan, K., Wang, Y., Sun, H., Fan, Y., Gandhi, V., Arnold, L.A., and Peng, X., J. Med. Chem., 2018, vol. 61, p. 9132. https://doi.org/10.1021/acs.jmedchem.8b00559

    Article  CAS  Google Scholar 

  20. Siegel, R.L., Miller, K.D., Fuchs, H.E., and Jemal, A., CA Cancer J. Clin., 2022, vol. 72, p. 7. https://doi.org/10.3322/caac.21708

    Article  Google Scholar 

  21. Rstakyan, V., Akopyan, A., Baltayan, A., Attaryan, H., Asratyan, G., Russ. J. Gen. Chem., 2015, vol. 85, p. 1191. https://doi.org/10.1134/S1070363215050333

    Article  CAS  Google Scholar 

  22. Masyuk, V.S., Kozyrkov, Y.Y., and Mineeva, I.V., Russ. J. Org. Chem., 2021, vol. 57, p. 1563. https://doi.org/10.1134/S1070428021100018

    Article  CAS  Google Scholar 

  23. Neufeld, B.H., Tapia, J.B., Lutzke, A., and Reynolds, M.M., Anal. Chem., 2018, vol. 90, p. 6867. https://doi.org/10.1021/acs.analchem.8b01043

    Article  CAS  Google Scholar 

  24. Huang, H., Li, Y.Y., and Li, H.R., J. Struct. Chem., 2021, vol. 62, p.1464. https://doi.org/10.1134/S002247662109016X

    Article  CAS  Google Scholar 

  25. Yang, Z., Liu, Q., Liu, Y., Qi, X., and Wang, X., RSC Adv., 2021, vol. 11, p. 10582. https://doi.org/10.1039/d0ra10563e

    Article  CAS  Google Scholar 

  26. Kumar, R., Saneja, A., and Panda, A.K., Methods Mol. Biol., 2021, vol. 2279, p. 213. https://doi.org/10.1007/978-1-0716-1278-1_17

    Article  CAS  Google Scholar 

  27. Liang, Y., Huang, W., Situ, Q., Su, W., Qiu, W., Li, S., He, L., and Chen, J., Russ. J. Gen. Chem., 2022, vol. 92, p. 725. https://doi.org/10.1134/S1070363222040144

    Article  Google Scholar 

  28. Yasuoka, Y., Fukuyama, T., Izumi, Y., Yamashita, T., Nakayama, Y., Inoue, H., Yanagita, K., Oshima, T., Yamazaki, T., Uematsu, T., Kobayashi, N., Shimada, Y., Nagaba, Y., Mukoyama, M., Sato, Y., Sands, J.M., Kawahara, K., and Nonoguchi, H., Heliyon, 2020, vol. 6, p. e05389. https://doi.org/10.1016/j.heliyon.2020.e05389

  29. Oki, K., Takase, M., Mori, S., and Uno, H., J. Am. Chem. Soc., 2019, vol. 141, p. 16255. https://doi.org/10.1021/jacs.9b09260

    Article  CAS  Google Scholar 

  30. Bedard, N., Foley, C., Davis, G.J., Jewett, J.C., and Hulme, C., J. Org. Chem., 2021, vol. 86, p. 17550. https://doi.org/10.1021/acs.joc.1c01280

    Article  CAS  Google Scholar 

  31. Gralewska, P., Gajek, A., Rybaczek, D., Marczak, A., and Rogalska, A., Cells, 2022, vol. 11. https://doi.org/10.3390/cells11121889

  32. Zhang, M., Yan, H., Li, S., and Yang, J., Brain Res., 2022, vol. 1790, p. 147961. https://doi.org/10.1016/j.brainres.2022.147961

    Article  CAS  Google Scholar 

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Funding

This work was funded by the GuangDong Basic and Applied Basic Research Foundation (2019A1515110313), Science and Technology Plan Project of Zhanjiang City (2019A01012, 2021A05045), Program for Scientific Research Start-up Funds of Guangdong Ocean University (R19057) and College Students Innovation and Entrepreneurship Training Program of Guangdong Ocean University (CXXL2022175).

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Authors and Affiliations

  1. College of Chemistry and Environment, Guangdong Ocean University, 524088, Zhanjiang, China

    Yuanwei Liang, Chengpeng Li & Wenhua Qiu

  2. Agricultural Product Processing Research Institute, Chinese Academy of Tropical Agricultural Sciences, 524001, Zhanjiang, China

    Puwang Li & Ziming Yang

  3. College of Food Science and Technology, Guangdong Ocean University, 524088, Zhanjiang, China

    Haisheng Lin & Yuntao Zhao

  4. Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, 524088, Zhanjiang, China

    Haisheng Lin & Yuntao Zhao

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  1. Yuanwei Liang
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  2. Chengpeng Li
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  3. Wenhua Qiu
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  4. Puwang Li
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Correspondence to Haisheng Lin or Yuntao Zhao.

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Liang, Y., Li, C., Qiu, W. et al. Nitrogen Mustard Based 2-Benzylidene-1-tetralone as ICT-Based Fluorescent Probe for Drug Release Monitoring and Cervical Cancer Therapy. Russ J Gen Chem 92, 2544–2552 (2022). https://doi.org/10.1134/S1070363222110433

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